Studies of vitamin D oxidation. 4. Regio- and stereoselective epoxidation of vitamin D

Regio- and stereoselective epoxidations of vitamin D sub(3) at the 7,8- and 5,6-double bonds were performed. Epoxidation with m-chloroperbenzoic acid gave exclusively (7R)-7,8-epoxyvitamin D sub(3) while epoxidation with tert-butyl hydroperoxide catalyzed by VO(acac) sub(2) afforded (5S)-5,6-epoxyvi...

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Bibliographic Details
Published in:Journal of organic chemistry 1984-05, Vol.49 (9), p.1537-1539
Main Authors: Nakayama, Keiko, Yamada, Sachiko, Takayama, Hiroaki, Nawata, Yoshiharu, Iitaka, Yoichi
Format: Article
Language:English
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Summary:Regio- and stereoselective epoxidations of vitamin D sub(3) at the 7,8- and 5,6-double bonds were performed. Epoxidation with m-chloroperbenzoic acid gave exclusively (7R)-7,8-epoxyvitamin D sub(3) while epoxidation with tert-butyl hydroperoxide catalyzed by VO(acac) sub(2) afforded (5S)-5,6-epoxyvitamin D sub(3) in excellent yield (90%). The structures of the epoxides were confirmed by spectral analysis and by single-crystal X-ray analysis.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00183a012